The preparation of secondary aliphatic diazo-compounds from hydrazones

Abstract

Several reports to the contrary notwithstanding, 2-diazopropane is neither difficult to prepare nor unduly unstable. It was made by oxidation of acetone hydrazone with mercuric oxide, as originally described by Staudinger and Gaule in 1916 except that base-catalysis was found to be essential. The analogous preparation of 4-diazo-octane is also described. The requisite hydrazones could be obtained in good yield if conditions conducive to disproportionation were avoided.